Author Topic: Will KMnO4 oxidise an allybenzene  (Read 805 times)

0 Members and 1 Guest are viewing this topic.

Antibody2

  • Guest
Will KMnO4 oxidise an allybenzene
« on: June 03, 2002, 04:15:00 PM »
will KMnO4 oxidise an allybenzene to its benzaldehyde, or does the allybenzene need to be isomerized  to a propenylbenzene first? Any thoughts on how to reduce solvent volume on this rxn would be also be appreciated.

thanks as always :)

Chromic

  • Guest
Sure
« Reply #1 on: June 03, 2002, 06:38:00 PM »
Sure it will, but it will happen at the wrong position. Every synthesis I've seen wants to make a 1,2-glycol or epoxide or acetyl/formyl glycol, not the 2,3-glycol etc. (I would expect a 2,3-glycol to rearrange to the terminal ketone (ie aldehyde) but maybe you'd get a 2-propanone? more input needed on that topic...) Without access to good analytical equipment, I think I'd choose to isomerize to be safe.

Reducing solvent volume should be easy, accomplished by slowly dripping a more concentrated solution of KMnO4 onto the solution. More experimental details are needed on that area, I haven't seen anyone attempt it yet.

Vibrating_Lights

  • Guest
Why
« Reply #2 on: June 03, 2002, 08:37:00 PM »
Why would you want a benzaldehyde instead of a ketone? Trying to explore a  new PEA.
VL_

Antibody2

  • Guest
Trying to explore a new PEA.
« Reply #3 on: June 03, 2002, 09:15:00 PM »
Trying to explore a new PEA. or the hypothetical viability of one.

chromic - yah, its just such a lousy yeilding rxn, that it seems more attractive if it could be done with a raw material. Adding two steps adds 40% to overall process.